1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-5-methoxy-1H-indole | 1325211-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-5-methoxy-1H-indole
• 英文别名: 1H-Indole, 5-methoxy-3-(1-methyl-3-pyrrolidinyl)-1-(phenylsulfonyl)-；1-(benzenesulfonyl)-5-methoxy-3-(1-methylpyrrolidin-3-yl)indole
• CAS: 1325211-74-2
• 化学式: C₂₀H₂₂N₂O₃S
• 分子量: 370.472
• InChiKey: RWJGYVBFADNMBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 在 lithium aluminium tetrahydride 、 sodium hydride 、 magnesium 、 碘甲烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 1-(benzenesulfonyl)-3-(1-methylpyrrolidin-3-yl)-5-methoxy-1H-indole
  参考文献：
  名称：

  Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands

  摘要：

  A series of N-1-arylsulfonyl-3-(pyrrolidin-3-yl)-1H-indole and N-1-arylsulfonyl-3-(4-chloro-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole derivatives (tryptamine derivatives with rigidized side chain) have been prepared and tested for their binding affinity to 5-HT6 receptor. Several compounds displayed potent binding affinity for the 5-HT6 receptor when tested in in vitro binding assay. The primary SAR indicates that rigidification of dimethylamino alkyl chain at C-3 of indole carbon maintains the binding affinity to 5-HT6R. The lead compound N-1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole, 10a (K-b = 0.1 nM) has shown excellent in vitro affinity and was active in animal models of cognition like NORT and water maze. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.106

文献信息

• Rigidized 1-aryl sulfonyl tryptamines: Synthesis and pharmacological evaluation as 5-HT6 receptor ligands
  作者：Ramakrishna Nirogi、Adireddy Dwarampudi、Ramasastry Kambhampati、Venugopalarao Bhatta、Laxman Kota、Anil Shinde、Rajesh Badange、Pradeep Jayarajan、Gopinadh Bhyrapuneni、P.K. Dubey

  DOI：10.1016/j.bmcl.2011.05.106

  日期：2011.8

  A series of N-1-arylsulfonyl-3-(pyrrolidin-3-yl)-1H-indole and N-1-arylsulfonyl-3-(4-chloro-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole derivatives (tryptamine derivatives with rigidized side chain) have been prepared and tested for their binding affinity to 5-HT6 receptor. Several compounds displayed potent binding affinity for the 5-HT6 receptor when tested in in vitro binding assay. The primary SAR indicates that rigidification of dimethylamino alkyl chain at C-3 of indole carbon maintains the binding affinity to 5-HT6R. The lead compound N-1-benzenesulfonyl-3-(4-chloro-1-methyl-2,5-dihydro-1H-pyrrol-3-yl)-1H-indole, 10a (K-b = 0.1 nM) has shown excellent in vitro affinity and was active in animal models of cognition like NORT and water maze. (C) 2011 Elsevier Ltd. All rights reserved.